tagCelebrities & Fan FictionCourting Brooke Shields

Courting Brooke Shields


I work in Los Angeles for a livery company. Due to a well deserved reputation for competence and discretion, our services are often utilized by many of the celebrity personalities living and working in the Los Angeles area. In my case, it also led to some amazing sexual encounters. Now, I don't pretend to claim that every beautiful woman that ever rode in my limousine tore off both our clothes, but in this forum there isn't much sense in writing about the ones "who got away". I'd rather make known the tales about the tails I've known.

Once such encounter took place when I was contracted to drive Brooke Shields for the evening. It was shortly after her split from Andre Agassi. I had been assigned to pick her up after her daily shoot for her TV series "Suddenly Susan".

As requested, I was at the studio at the end of the days filming. It was early on a Friday evening and Miss Shields requested to be driven to a Santa Monica restaurant popular with many of the upscale personalities in Southern California. We reached the restaurant about 5:30 and I was told to be back at the door at 7:30.

I took advantage of the time to have my own dinner before returning to perform my chauffeuring duties. When I returned at the appointed time, Miss Shields was nowhere to be seen. Assuming that her dinner engagement had run late, I parked nearby and relaxed in the limousine. After a half hour, I received a call from our dispatcher, ordering me to pickup my passenger at the rear entrance of the eatery. This was not an uncommon request as all too often the paparazzi will be tipped to the presence of a celebrity. In many of those cases, the celebrity's desire for privacy will prompt a change in plans.

I started the auto and drove around the corner and up a back alley until I was behind the establishment. Almost immediately, the maitre d' escorted Miss Shields out to the car. I was already holding the door open and he quickly assisted her into the car. The whole thing took less than a minute, but I had time to see that my passengers face was red and it appeared she had been crying.

The maitre d' made a furtive motion that was obviously meant to convey that I should stay silent, which indicated to me that she was definitely trying to avoid media attention. The maitre d' then quickly whispered that her dinner companion had not shown up and she suddenly burst into tears at her table. Luckily she had been in a private alcove and at her request he had helped her leave the restaurant without anyone else seeing her.

This was far from the first time I had been entrusted with keeping such an occurrence quiet and it seemed like just another evening so far. Things, however, were to end under far from normal circumstances.

I returned to my position in front of the car and pulled away from the alley. Switching on the intercom, I inquired as to our next destination. She choked back a sob and asked me to just drive north on the Coast highway for a little while. I cruised along the road for about 20 minutes, enjoying the sunset and making good time on the road.

It was about then that her voice came over the intercom and she haltingly asked me to pull into one of the scenic overlooks that allows a rather spectacular view of the Pacific Ocean. It was almost dark by now and I assumed she wanted to get some fresh air and felt that she was in much less danger of being recognized. I wheeled into the next stop and parked the car.

I stepped to the door and held it open as she exited. She seemed in control of herself but of course I knew that could be an act. As this particular overlook was just above a steep drop, I followed a few steps behind as she slowly walked over to the rail.

In the rapidly dwindling twilight, it was difficult to read her expression when she turned and asked me my name. I introduced myself and she sniffled and said, "Well, it looks like it's just you and me tonight, Henry. First I got dumped by my husband and now I get stood up by my date."

She sounded rather pitiful and I found myself feeling sorry for her. I am one of those people who never know what to say and as I racked my brain for an appropriate expression of sympathy, she interrupted my thoughts with a request for a cigarette.

I don't smoke myself but part of providing excellent service is being prepared for such requests, so it was easy enough to fetch a smoke and a light from the car. We stood there in silence while she finished about half the butt. She was obviously not a regular smoker as she coughed several times. It was a pretty sad sight and if she hadn't been so visibly depressed, I might have started laughing. As it was, I simply maintained my silence.

Suddenly she seemed to perk up a bit. She headed back to the car and told me she was ready to leave. I slid behind the wheel and got the car in motion. Unlike before, she asked me to lower the tinted glass divider between me and the passenger compartment "so we can talk."

This was far from a typical situation as most (but not all) of the celebrities I had chauffeured in the past had seen me more as a part of the car than as a person. It was a nice change to be treated like this and I said so, hoping it wouldn't make her change her mind.

To my relief, she laughed and asked me how I had come to be a limousine driver. I gave her the two minute version, thinking she had asked only to be polite. To my surprise however, she prompted me for more information, asking about the small town in which I grew up. She truly seemed interested in my response and I felt more and more as if I was on a first date, with the odd twist of my partner riding in the backseat instead of along side me.

In return for my story, Brooke (as she had told me to call her) shared a few tales of behind the scenes events, all of which where humorous, often with her as the one looking silly. I was impressed with her ability to laugh at herself and found myself becoming enchanted with her to a degree beyond her physical attractiveness. I actually began to forget that she was relatively famous and started to think more of her as a friend.

We began trading stories, with me relating some of the funnier episodes I had witnessed, such as the couple that had sex in the car without realizing the intercom switch was on or the star couple who got so drunk I had to pull over so they could toss their cookies by the side of the road. I was careful not to mention any names but she enjoyed them anyway.

About forty five minutes later, she suddenly said she was hungry and asked me to pull into the parking lot of a pizza parlor we were passing. At her request, I went in and ordered a pizza and waited twenty minutes or so until it was ready. She apologized for not getting out and I assured her I understood her desire for anonymity.

Soon enough we were back on the road and she directed me to a nearby park. Once the car was parked, she stepped out and I carried the pizza to a picnic table. Still in the mind frame of employee, I hung back until she insisted I sit down and eat with her. I wasn't really hungry but to be polite (and allow myself to further enjoy her company), I sat down and nibbled on a slice while she dug in. We continued to chat about Los Angeles and the people we had encountered.

By the time she was finished eating, it was almost ten o'clock and she directed me to her Bel Air mansion. I pulled into the driveway and helped her from the car. As I escorted her to the door, she slipped her arm into mine and leaned her head against my shoulder. She fumbled in her purse for the keys and trying to be gallant, I took them from her and opened the door.

I expected at this point to be thanked and sent on my way but Brooke pulled me towards her then leaned in close and kissed me. I was somewhat surprised but figured she felt much as I did, namely that we had passed a friendly evening together. Her next words shocked me.

"Henry, you have had contact with a lot of famous women. Tell me, have you ever fucked any of them?"

To this point I had only had one such encounter (with actress/model Elizabeth Hurley) and I wondered how to answer. However, before I could say anything, she spoke again.

"Never mind. You are a gentleman and a gentleman wouldn't say anything anyway. It doesn't really matter if you have or haven't, but I'm hoping you'll fuck me tonight."

I was stunned that she would be so blunt but definitely willing to fulfill her wish. She could tell I was obviously unsure what to do and so she took the initiative. She leaned in close to me and pressed her lips against mine. I confess I was a bit tense but quickly began to relax. Brooke pushed things forward by sliding her tongue between my lips and we held each other tightly as we shared a long French kiss.

As the kiss ended, she pulled me into the house and the door swung closed behind us. We kissed again before she moved her lips along my neck towards my shirt collar. I held her ass in my hands and pulled her crotch against mine. By now I was erect and she could obviously feel my hard-on pressing against her.

In spite of my excitement, I found myself wondering why she was doing this. I mean, she was a well-known entertainer and I was simply a chauffeur. I pulled away just a bit and she looked up at me, an expression of curiosity in her eyes. While I searched for a way to state my concerns without spoiling the mood, she solved my dilemma for me.

"Henry, we are both adults. No, this isn't a standard procedure for me. Yes, I am lonely and a little depressed. But I'm not doing something I wouldn't do had we met under different circumstances. We aren't likely to find ourselves together again so lets just share the time we have together."

Well, those words were just what I needed to hear. During her little speech, Brooke had pulled my shirt from my trousers and undone the buttons to my waist. Leaning back in, she began kissing my chest while her hands fumbled at my belt. Sure now that I wanted to continue, I pushed her hands away and opened my belt and unsnapped my pants.

Her hands now found my hard-on and she gave it a firm squeeze. My cock leaped in her hand as if it had a mind of its own and she giggled delightedly. I kicked my shoes off and slipped my shirt from my shoulders as she worked my pants down to my ankles, kneeling so she could pull them off. In just a few seconds, I was standing naked before her. Her eyes roamed up and down my body and she nodded approvingly.

I reached for her but she stepped away from me. She unbuttoned her own blouse and pulled it off. Then she unzipped her skirt and let it fall to join her blouse in a pile on the floor. Standing before me in a strapless bra and cotton panties, she looked good enough to eat. I vowed to myself that I would do just that as soon as the opportunity arose.

She reached behind herself to unsnap her bra and allowed her tits to spill free. They were well formed and stood proudly on her chest. The nipples were dark brown and fully erect. She noticed my gaze and told me she enjoyed having a lover suck and nibble on them.

Her frank talk and physical beauty were rapidly increasing my excitement and I moved forward to hug her against me. We began kissing frantically, our hands roaming over each others bodies. I could feel my cock working its way between her legs and she opened them slightly to squeeze my dick between her thighs. As we were of near equal height, this put her pussy directly atop my erection, with only the thin fabric of her panties between us.

We continued to make out standing there in her front hallway. Her cunt was rubbing against the top of my prick and we both began breathing harder. Her hands slid down to hold the cheeks of my ass and she used the pressure to pull us even more closely together.

I moved my lips from her mouth to her neck, kissing my way down to her bare shoulders. I licked and sucked the skin there before continuing down her chest to her tits. I licked around her left nipple, then sucked in into my mouth. Brooke moaned deeply in response and gripped my ass even tighter. I repeated the action on her right nipple and she increased the motion of her pussy on my cock.

The sensation of the cotton rubbing against my dick was incredible. I began to worry that I would cum right there, before we got past the foreplay. To avoid this, I let my lips return to their exploration of her body. I backed off slightly and kissed my way down her belly until I reached the waistband of her panties. She was standing with her legs slightly spread and her hands were twisted into my hair.

My fingers slid up her thighs and into the front leg holes of her underwear. I could feel the heat of her cunt and when I let my hands slide between her thighs, I could feel the moisture that had soaked the crotch of her panties. I slowly began to slide them off her hips.

Her pussy juice had made them so sticky that they clung to her cunt lips, and as they peeled away from her sex, I could see the moisture begin to run down her leg. I slid them down to her feet and tossed them aside after she stepped free. I planted kisses along her upper thighs and tried to work my tongue between her legs. As I did so, she pulled at my hair as if to stop me. Confused, I backed off so I could look up into her eyes.

"Not here," She explained with a smile. "Come with me."

I stood up and she took my cock in her hand, using it to tug me along behind her. She wasn't trying to hurt me, just lead me to whatever destination she had in mind. We crossed through the back of her house and out the French doors that led into the large backyard.

As she led me across the yard to the pool, she used her thumb to rub the tip of my cock, spreading the pre-cum around the head and causing even more moisture to gather at the slit. She had me collect a cushion from one of the lounge chairs and she took a towel from the cabana. Then she led me to a large fenced area and paused in front of a gate.

With a light kiss on my cheek, Brooke whispered that this was the tennis court her tennis pro husband had built. It had gone unused since he left and she had it in mind to play a different type of game there.

We entered the court and she led the way to the exact center of the area, where the net would have been if the court were ready for it's traditional use. This was the first time I had gotten a good look at her from behind. Her hair was longish at the time, flowing down past her shoulders to lay on her upper back. Her ass was firm and round and her legs where muscular but not overly so. All in all, she made a very sexy sight, sensuously walking across the moonlit court.

She turned when she realized I wasn't following her. Grinning seductively, she cupped her tits in her hands and slid her tongue across her lips. Entranced, I moved towards her, only to stumble forward and trip over the cushion I was carrying. I didn't fall to the ground, but in trying to keep my balance, I half ran, half fell to the middle court area where she was standing. I didn't slam into her, but neither did I approach her in any type of control. I actually bumped up against her hard enough to force her to take a single step back to maintain her own footing.

I felt like an idiot in my embarrassment but Brooke refused to let it spoil the mood. She laughed and pushed me gently back towards the cushion I had dropped. In two steps, I was straddling the cushion. She gracefully dropped to her knees on the cushion and placed a kiss on the tip of my cock.

She moved her hands to my hips to give herself some balance and took the head in her mouth. My dick pulsed as her tongue slid across the underside and I moaned with pleasure at the sensation. She worked more of the length into her mouth and slowly let it slide back out. She continued to stimulate me this way for several minutes. Then she began to move faster, taking me deeper each time. The combination of her saliva and the pre-cum that was now flowing steadily provided sufficient lubrication that she was soon taking the entire length in her mouth, her nose bumping gently into my pubic hair each time she did so.

She stopped her sucking and began to use her tongue on me. She would lick down the underside then back up again, repeating the motion on the sides and top. Then she swirled her tongue across the head and tickled the tiny slit with the tip of her tongue. Then she took me back into her mouth and swallowed the length once more.

She began sucking me with a steady rhythm now and I could feel my balls tighten as my orgasm neared. I put my hands on her head to help keep me from falling as my knees weakened. She kept up her deep throat technique and my cock began to pulse, sending spurt after spurt of cum into her throat. She swallowed it all down without hesitation and continued to suck even after my ejaculation was complete. I finally had to push her away from my crotch so I could sink to my knees.

Brooke pushed her tits forward so they were directly in front of my mouth and I reflexively took a nipple into my mouth. She curled her hands around my head and kept my face pressed against her chest. I licked and sucked both her nipples in turn, occasionally turning my attention to her tits themselves. I kept at this for five or six minutes, which allowed my legs some time to regain some strength. By the time I was ready to do more than lap at her tits, her entire chest was covered with my spit and she was ready for more direct stimulation.

I gently guided her backwards until she was lying on her back on the cushion. I straddled her with my body and we kissed deeply, our tongues sliding in and out of each others mouth. Then I began to kiss my way down her body until my head was positioned between her upper thighs and her cunt lay dripping before me.

Her thighs were smeared slick and I lapped at the sweetness that had collected there. Once I had licked her thighs clean, I planted a kiss on her pussy and let my tongue lick up the length of her slit. Her cunt lips parted slightly and I ran my finger from the bottom of her pussy to the top and back down again. Liquid began to run from her once more and I eagerly began to eat her.

She moaned and thrashed on the cushion as I did so. Each time my tongue grazed her clit, her hips bucked upwards. She entwined her fingers in my hair and directed my head so my mouth was center over the hardened nub. I sucked it into my mouth and let my tongue dance back and forth over her clit. She continued to moan and move about but her firm grip kept my mouth glued to her. I sucked and licked her continuously for about ten minutes, her movements and gasps become more and more aggressive. Finally she began to beg me to make her cum.

"Yes, that's it. Do it, do it. Make me cum for you. Suck my pussy until I cum. Keep it up. Don't stop. Use that tongue!"

I began to manipulate her clit faster and let my index finger find the folds of her pussy. I slowly pumped my finger in and out in rhythm with her humping and moaning. At last she began to cum. Her moans turned to gasps and groans and her crotch was actually lifting off the cushion as her orgasm swept through her. I felt the muscles of her cunt squeezing my finger and the juices from her hole ran down my finger to coat my hand. She gave a final moan that that rose into a half scream and fell still.

I let my finger slide slowly from her and began to pull away from her. She pulled forcefully on my hair and told me to fuck her.

"Please, put your cock in me. Give me a ride. I need you in my cunt, need it now. Fuck me hard."

I moved up so my dick was at the entrance to her pussy. Brooke pulled her legs up towards her chest to allow me full access. I rubbed my cockhead along her pussy and then I entered her. She was extremely wet and my cock penetrated her fully without any resistance.

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